Interrupting the Nazarov Cyclization with Indoles
نویسندگان
چکیده
منابع مشابه
Catalytic formal Homo-Nazarov cyclization.
The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic, and carbocyclic compounds were obtained under mild conditions using Brønsted acid catalysts. Preliminary investigation of the reaction mechanism indicated a stepwise process.
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Transition metal free Brønsted acid mediated synthesis of biologically important pyrido[1,2-a]indole scaffolds through aza-Nazarov type cyclization of readily available diaryl(2-pyridyl)methanol using formic acid has been developed. This methodology has been successfully extended to synthesize atropisomers.
متن کاملConquering the Challenges of the Nazarov Cyclization
One of the most powerful synthetic transformations with the ability to stereospecifically create new carbon-carbon bonds by simple orbital reorganization are electrocyclic reactions. One of the most recognized electrocyclic reactions is known as Nazarov cyclization. This reaction involves the conversion of divinyl ketones to cyclopentenones by activation with a Brønsted or Lewis acid. It was or...
متن کاملFormal homo-Nazarov and other cyclization reactions of activated cyclopropanes.
The Nazarov cyclization of divinyl ketones gives access to cyclopentenones. Replacing one of the vinyl groups by a cyclopropane leads to a formal homo-Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization of vinyl-cyclopropyl ketones is a stepwise process, often requiring harsh conditions. Herein, we describe two different approaches for furth...
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Cyclopentadienyl, hydrinedienyl, and indenyl glycines were synthesized using dienylaziridines as Nazarov cyclization precursors for the first time. Several substrates were synthesized to demonstrate the compatibility of this reaction. Asymmetric synthesis of these amino acids was also developed to show the additional scope of this method.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2008
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol801587u